Sodium Bicarbonate → HCID 24905251, compound

HRID 731774Notes

Reaction equation

HRID 731774 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:27]([CH3:29])[CH3:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[C:13]([O:25][CH3:26])[CH:12]=3)[C:3]=12.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O.O>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([CH:27]([CH3:28])[CH3:29])[N:9]=2)=[CH:12][C:13]=1[O:25][CH3:26]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 24905150HCID 24905150, compound

Product 1

HCID 24905251HCID 24905251, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenylcarbamate (BA20) (20 mg, 0.05 mmol) in CH2Cl2, TFA, S(CH2)2, H2O (45:45:5:5) (1 mL) was stirred at room temperature for 15 minutes. NaHCO3 (2 mL) was added till reaction was alkaline. Reaction was extracted with H2O and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA20d.

Workup

  1. customReaction
  2. extractionwas extracted with H2O and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)
  5. customto yield BA20d

Sources & evidence

ORD record
ord-6591cb0568e6429980a77bdc755bfeaf
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

Loading…